Enantioselective Synthesis of Chiral 3‐Alkynyl‐3‐Hydroxyindolin‐ 2‐Ones by Zn/bis(Sulfonamide)‐Diamine Catalyzed Asymmetric Addition of Alkynes to Isatins. Issue 7 (1st June 2022)

• Record Type: Journal Article
• Authors: Qu, Hongmin; Chen, Yu; Ceng, Xiangling; Tang, Pei; Wang, Huijing; Chen, Fener
• Is Part Of: Asian journal of organic chemistry. Volume 11:Issue 7(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-01
• Subjects: alkynylation -- chiral 3-alkynyl-3-hydroxy-2-oxindoles -- chiral bis(sulfonamide)-diamine ligand -- isatins -- metal catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200188
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The catalytic enantioselective alkynylation of isatins, catalyzed by a Zn(OCOCF3 )2 /chiral bis(sulfonamide)‐diamine (BSDA) catalyst under mild condition, has been developed. The desired chiral 3‐alkynyl‐3‐hydroxy‐2‐oxindoles were obtained in moderate to excellent yields (up to 96%) and good to excellent enantioselectivites (up to 97% ee ). The reaction is broad in scope with respect to aryl‐substituted terminal alkynes and substituted isatins. Abstract : The catalytic enantioselective alkynylation of isatins, catalyzed by a Zn(OCOCF3 )2 /chiral bis(sulfonamide)‐diamine (BSDA) catalyst under mild condition, has been developed. The desired chiral 3‐alkynyl‐3‐hydroxy‐2‐oxindoles were obtained in moderate to excellent yields (up to 96%) and good to excellent enantioselectivites (up to 97% ee ). The reaction is broad in scope with respect to aryl‐substituted terminal alkynes and substituted isatins.